Regarding 2: Alignment discussion is explicitly barred from the D&D/PF thread.
1: Honestly? You could probably make a good argument for any of those alignments.
LN: He's not taking lives for any nefarious or pointless reasons, but as part of a worldview which sees killing as a business transaction, as a legitimate element of the social order. He doesn't kill because he's crazy or wants to raise a mount of corpses for his evil god or whatever, but because it's profitable. Fantasy corporate capitalist.
LE: Those people are obviously less important than him in the social hierarchy; it's only natural that their lives be one of the many things he can use or take if he wills it. Fantasy authoritarian dictator.
CN: Murder may be illegal, but the rules set down by society or some noble don't apply to him if he doesn't want them to. He's good at killing and can make a living doing it, so he's under no externally imposed obligation to hesitate from doing so. Fantasy libertarian hitman.
That's just ten-second soundbite justifications for any of those. This sort of thing is why I think that people who call the D&D alignment chart inflexible, shallow, &c. must be really dull and unimaginative. It's all in the details. An alignment is like a Worm parahuman power rating: a two-word off-the-cuff summary of the general thrust of how the character sees and interacts with the world, not a substitute for a real personality.